Vacation rentals with a pool in Cayman Islands

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Cayman Islands

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Condo in Savannah

4.96 out of 5 average rating, 72 reviews

Beachfront walkout with amazing patio & view

The ultimate beach paradise is literally right outside your door! Wake up with coffee and the sun rising over the sea. Spend the day snorkeling to the reef or sunbathing under a palm tree on the sand. Chill with oceanside cocktails at sunset in the screened in patio or enjoy a shell treasure hunt at low tide with the kids! Coral Bay Villa, a beautiful, spacious and bright two bedroom is centrally located on a gorgeous virtually private white sand beach in Spotts close to shops and amenities.

Guest favorite

Cottage in West Bay

4.99 out of 5 average rating, 221 reviews

Luxury Cottage, 1bd/1ba steps to Pool+7 Mile Beach

Our Queen Cottages are part of the Botanica collection of award winning island style cottages. This unit has a private outdoor dining and garden shower. At Botanica, our focus is on casual luxury, dreamy details and high end amenities. Property highlights includes a resort style pool with heated spa set in a tropical oasis. We also offer a complimentary shuttle in our vintage Land Rover Defender to nearby beaches. Be sure to check out our other listings under my profile. Non Smoking Complex

Guest favorite

Rental unit in East End

4.93 out of 5 average rating, 14 reviews

Spacious Beachfront Penthouse Studio (Sleeps 2)

Located in East End, this privately owned penthouse studio at the Wyndham Reef Resort boasts an unbeatable oceanfront view along a pristine sandy beach. It has three swimming pools and a hot tub, a lively bar, restaurant with daily menus, coffee shop, onsite laundry, diving, nightly entertainment, snorkelling, spa, and fitness centre. This large studio has a king size bed, luxury bathroom, flat screen TV, kitchenette with microwave and fridge and a patio overlooking the beach for sunset drinks.

Guest favorite

Home in Stake Bay

5 out of 5 average rating, 47 reviews

Modern Oceanfront, 2Primary Suites, sleeps 6, pool

We offer a Hurricane Worry-free Guarantee. Only a short 25-minute flight from Grand Cayman, this newer home provides stunning oceanfront vistas with all modern amenities to enjoy barefoot luxury. Large windows and the open concept floor plan allow for breathtaking views of the pool and sea and include a fully-equipped kitchen, dining, and living areas. Also overlooking the ocean are two master king-size bed suites with tiled baths. A third bedroom has a queen bed and views of tropical foliage.

Guest favorite

Condo in Grand Harbour

4.93 out of 5 average rating, 230 reviews

The Sanctuary serene Grand Harbour view 2Bed/2Bath

Cool clean contemporary Sanctuary with water views; a two bedroom/two bathroom condo with a full kitchen and living room packed with all popular amenities (wifi, cable television, Apple TV, Netflix, Playstation game console, central A/C, iron and ironing board, washer and dryer, outdoor patio, pool and free parking) - conveniently located in Grand Harbour. The Shoppes at Grand Harbour, & Harbour Walk are next door. Perfect for exploring and enjoying all that the Cayman Islands has to offer.

Guest favorite

Condo in George Town

4.94 out of 5 average rating, 166 reviews

Cayman Reef Resort on Seven Mile Beach

At the heart of Seven Mile Beach, our home is in the middle of everything and far from nothing. Extensively renovated and well maintained, the condo is designed for you to enjoy a tranquil beach getaway in a luxurious setting with all the comforts of home. Picture perfect views, top of the line amenities and our local touch provide a warm welcome and cozy stay. We are fully licenced and our rate includes the 13% tourist accommodation tax. 20% discount from list price for local residents!

Guest favorite

Guesthouse in Cayman Islands

5 out of 5 average rating, 41 reviews

Tua'r Mor (near the sea) quiet waterfront escape.

This lovely one-bedroom, one-bath charismatic bungalow is located in the quiet neighborhood of Sunrise Landing, Newlands, and is perfect for couples or small families. Tua’r Mor provides everything you need to feel at home, with an open kitchenette and dining/living area. The unit has everything from beach towels, beach chairs, and coolers so you can enjoy a day out. A hammock awaits you in your own private garden, overlooking the canal, where you can enjoy watching the sun rise or set.

Superhost

Condo in George Town

4.85 out of 5 average rating, 135 reviews

Grandview condominium directly on 7-mile beach

This family friendly condo is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love this place because of the location, the people, the ambiance, the outdoors space, and the neighborhood. My place is good for couples, solo adventurers, business travelers as well as families with children. The property has biggest pool on Seven Mile Beach and hot tub overlooking beach with best sunsets. It also offers tennis courts and Basketball.

Guest favorite

Guest suite in Savannah

4.98 out of 5 average rating, 215 reviews

Paradise Escape-Charming Oceanfront Guest Suite

A tranquil oceanfront escape for couples and solo adventurers... Ours is a unique community with quaint freehold condo cottages on a vast tract of oceanfront land. Wake-up in bed to a lovely view of a luscious green landscape that melds with the emerald green and blue ocean, sip a hot cup of coffee on the porch, enjoy a sunset cocktail by the ocean front pool, break a sweat in a friendly game of tennis, or take a blanket out to the lawn under the palm trees for breathtaking star gazing.

Guest favorite

Condo in Rum Point

4.93 out of 5 average rating, 123 reviews

Nature's View: Pools of the Kai #2

Discover the peaceful Caribbean paradise of Cayman Kai. This secluded oasis will put you at ease as soon as you walk through the door. Our beach front property features stunning views across the Caribbean Sea to an unspoiled nature reserve. The double story screened in private pool deck can't be beat. Perfect for family holidays or a romantic getaway. Savor heavenly mornings and sundowners on your master bedroom balcony. Stroll down the beach to Kaibo, true barefoot living!

Superhost

Condo in George Town

4.87 out of 5 average rating, 147 reviews

Beautiful Modern Condo on 7 Mile Beach

Welcome to our beautiful second floor condo on the world renowned Seven Mile Beach. Sunset Cove is a beachfront resort minutes from George Town. It has a stunning beach lagoon and amazing pool with a kiddies pool, hot tub and swim-up bar. Our “beach chic” condo has just been fully renovated. We stripped it back to the bare concrete floor and walls and everything is brand new. We hope you like it and look forward to welcoming you to our little island paradise!

Guest favorite

Rental unit in George Town

4.96 out of 5 average rating, 121 reviews

Flip Flop Villa

A superb location to all things fun makes this condo a great spot! Centrally located to Spotts Beach or Smith Cove Beach its only 10 mins away or George Town to Seven Mile Beach 15 mins away. Ideally located to explore both coasts. Out of the way of the hustle & bustle but close to it if you like. Two grocery, convenient stores and restaurants within a few mins.